AA 9908 then UA 1548 at O'Hare
Milwaukee → Chicago → Cleveland
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:45UA 1548 to Cleveland leaves the gate
20 h 55 apart on the timetable, overnight
UA 1548 leaves 20 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.